“Oxidative Dimerization of (Hetero)aromatic Amines Utilizing t‐BuOI Leading to (Hetero)aromatic Azo Compounds: Scope and Mechanistic Studies”

“Oxidative Dimerization of (Hetero)aromatic Amines Utilizing t‐BuOI Leading to (Hetero)aromatic Azo Compounds: Scope and Mechanistic Studies”
Sota Okumura, Chun-Hsuan Lin, Youhei Takeda*, and Satoshi Minakata*
J. Org. Chem.. 2013, 78, 12090–12105. DOI: 10.1021/jo402120w

Abstract: A straightforward synthetic method of both symmetric and unsymmetric aromatic azo compounds through an efficient and cross-selective oxidative dimerization of aromatic amines using tert-butyl hypoiodite (t-BuOI) under metal-free and mild conditions has been developed. This method was also found applicable to the synthesis of heteroaromatic azo compounds. The spectroscopic study indicates the involvement of N,N-diiodoanilines in the oxidative reaction as the key intermediate.